This invention relates to polycyclic compounds, a process for preparing these compounds, uses and pharmaceutical compositions thereof. More particularly this invention relates to certain derivatives of 4-azahexacyclo-[5.4.1.0.sup.2,6.0.sup.3,10.0.sup.5,9.0.sup.8,11 ] dodecane, a process for preparing such compounds, their use as pharmaceutical agents, and pharmaceutical compositions thereof.
Subsequent to the discovery of the antiviral an anti-Parkinsonistic properties of amantadine, considerable research has taken place to exploit the medicinal properties of polycyclic compounds. U.S. Pat. No. 3,449,422 describes certain amino derivatives of pentacyclo-[5.4.0.0.sup.2,6.0.sup.3,10.0.sup.5,9 ] undecane, such as the 8-amino derivatives (A), and their preparation as well as their activity against Asian and swine influenza viruses. In European Patent Application 82306975.2 it has been disclosed that the pentacvclo-undecane amines having structure (A) (referred to above) further-more exhibit anti-Parkinsonistic properties. ##STR2##
Antiviral properties have also been reported for a number of amino derivatives of polycyclic hydrocarbons related to A, or the so-called bird-cage type of compounds, for instance in U.S. Pat. Nos. 3,622,628; 3,536,761; 3,641,148; 3,532,741; 3,456,008 and 3,562,317.
In South African Patent 88/7542 it was demonstrated that derivatives of the amino ether (C), formed by reduction of the imino ketone (B) with sodium borohydride, exhibits useful calcium antagonistic properties. These findings, as regards the structure of the product, contradict a report by Sasaki et al. (Tetrahedron, 30, 2707, 1974) that under the same experimental conditions mentioned above the imino ketone is converted to the hydroxy-aza type compound (D).
Marchand et al. (J. Org. Chem., 53, 2644-2647) and later van der Schyf et al. (S. Afr. J. Chem., 42(1), 46, 1989) confirmed that the reduction product mentioned above was indeed the amino ether compound (C) and not hydroxy-aza compound (D). It was therefore found by the inventors of South African Patent 88/7542 that the structure of the product obtained by the reduction of compound (B) with sodium borohydride had previously been wrongly assigned by Sasaki et al.
A. P. Marchand and co-workers (J. Org. Chem., 53, 2644-2647, 1988) furthermore reported that only the hydroxy-aza compound (D) was obtained by reduction of the imino ketone (B) with sodium cyanoborohydride.
In order to illustrate the aforementioned, reference is made to the reaction scheme shown immediately hereunder. ##STR3##